Ammonium Chloride → HCID 67981274, compound

HRID 705379Notes

Reaction equation

HRID 705379 reaction equation
[I:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([N+:11]([O-])=O)=[CH:10][C:5]=2[O:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>[Fe].O1CCCC1.CO.O>[I:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[O:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 11588651HCID 11588651, compound

Product 1

HCID 67981274HCID 67981274, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

In a round bottom flask were combined 3-iodo-6-nitro-2-phenylbenzofuran (3.65 g, 10.0 mmol), ammonium chloride (0.802 g, 15.00 mmol) and iron powder (2.79 g, 50.0 mmol). To this was added a mixture of tetrahydrofuran/methanol/water (1:1:2 v-v, 100 mL). The mixture was heated to reflux for a total of four hours. After cooling to room temperature, the reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The organic layer was dried (Na2SO4) filtered and concentrated to give the title compound 3.35 gm (100%).

Workup

  1. customIn a round bottom flask were combined
  2. additionTo this was added
  3. temperatureThe mixture was heated
  4. temperatureto reflux for a total of four hours
  5. filtrationthe reaction mixture was filtered through diatomaceous earth
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was partitioned between water and ethyl acetate
  8. dry with materialThe organic layer was dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-6a38ae4e31bd49708ac074e1ba385f2c
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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